EP2838930A1 - Polymères contenant des unités oligo-triarylamine substituées et dispositifs électroluminescents contenant ces polymères - Google Patents

Polymères contenant des unités oligo-triarylamine substituées et dispositifs électroluminescents contenant ces polymères

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Publication number
EP2838930A1
EP2838930A1 EP13717171.6A EP13717171A EP2838930A1 EP 2838930 A1 EP2838930 A1 EP 2838930A1 EP 13717171 A EP13717171 A EP 13717171A EP 2838930 A1 EP2838930 A1 EP 2838930A1
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Prior art keywords
organic
polymer
structural units
substituted
atoms
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EP13717171.6A
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German (de)
English (en)
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EP2838930B1 (fr
Inventor
Holger Heil
Fabrice ECKES
Dominik Joosten
Anna Hayer
Katja STEGMAIER
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Merck Patent GmbH
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Merck Patent GmbH
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Definitions

  • the present invention relates to polymers comprising substituted oligo- 1- triarylamine repeating units, preferably bis-triarylamine
  • OLED Organic Light Emitting Diodes
  • Electroluminescent devices containing these polymers Electroluminescent devices containing these polymers.
  • OLED organic electroluminescent devices
  • OLEDs Components of different functionality needed.
  • the different functionalities are usually in different layers.
  • multilayer OLED systems include, but are not limited to, charge injecting layers, e.g. electron and
  • hole injecting layers e.g. Electron and hole-conducting layers, as well as layers on, the
  • CONFIRMATION COPY Lifespan, efficiency, etc. can be achieved.
  • Ar 1 to Ar 5 at each occurrence, each same or different, a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;
  • n 1, 2 or 3, preferably 1 or 2 and more preferably, the dashed lines being bonds to adjacent ones
  • Ar 2 and / or Ar 4 is in each case substituted in at least one, preferably in one of the two ortho positions, with Ar 6 , Ar 6 being a mono- or polycyclic, aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms which may be substituted by one or more R radicals and
  • Ar 4 and / or Ar 5 are each substituted in at least one, preferably in one of the two ortho positions, with Ar 6 , wherein Ar 6 is a mono- or polycyclic, aromatic or
  • heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals.
  • the substituent Ar 6 may be arranged either only on Ar 2 or Ar 4 or on Ar 2 and Ar 4 .
  • the substituent Ar 6 may be arranged either only on Ar 4 or Ar 5 or on Ar 4 and Ar 5 .
  • Ar 6 can either be linked directly, that is to say via a single bond, with Ar 2 and / or Ar 4 or Ar 4 and / or Ar 5 or else via a linking group X.
  • the structural unit of the formula (I) preferably has the structure of the following formulas (I-1a), (1-1b), (I-2a) and (I-2b):
  • r 0 or 1, preferably 0.
  • the at least one structural unit of the formula (1-1) of the polymer according to the invention is characterized in that Ar 2 and / or Ar 4 is in each case substituted by Ar 6 in one of the two ortho positions, and Ar 2 and / or Ar 4 is additionally linked in each case with Ar 6 in the meta position adjacent to the substituted ortho position.
  • the structural units of the formula (1-1) thus preferably have the structure of the following formulas (1-1 c) and (1-1 d):
  • n 0, 1, 2 or 3
  • polymer is to be understood as meaning both polymeric compounds, oligomeric compounds and dendrimers.
  • the polymeric compounds of the present invention preferably have from 10 to 10,000, more preferably from 10 to 5000, and most preferably from 10 to 2000 structural units (i.e., repeating units).
  • the oligomeric compounds according to the invention preferably have 3 to 9 structural units.
  • the branching factor of the polymers is between 0 (linear polymer, without branching points) and 1 (fully branched dendrimer).
  • the polymers of the invention preferably have one
  • the polymers according to the invention are either conjugated, partially conjugated or non-conjugated polymers. Preference is given to conjugated or partially conjugated polymers.
  • the structural units of the formula (I) can be incorporated according to the invention into the main or the side chain of the polymer. Preferably, however, the structural units of formula (I) are incorporated into the main chain of the polymer. When incorporated into the side chain of the polymer, the structural units of formula (I) may be either mono- or bivalent, i. they have either one or two bonds to adjacent ones
  • Polymers which in the main chain mainly sp 2 -hybridized (resp.
  • conjugated polymers may also be replaced by correspondingly hybridized heteroatoms.
  • conjugated when in the main chain for example arylamine units
  • Arylphosphinicaen certain heterocycles (ie conjugation of N, O or S atoms) and / or organometallic complexes (ie conjugation via the metal atom) are located.
  • conjugated dendrimers units such as simple alkyl bridges, (thio) ether, ester, amide or imide linkages are clearly defined as non-conjugated segments.
  • a partially conjugated polymer is to be understood as meaning a polymer which contains conjugated regions which are separated from one another by nonconjugated sections, targeted conjugation breakers (for example spacer groups) or branchings, for example in which longer conjugated sections in the main chain are replaced by non-conjugated segments.
  • Conjugated portions are interrupted, or containing longer conjugated portions in the side chains of a non-conjugated in the main chain polymer.
  • Conjugated and partially conjugated polymers may also contain conjugated, partially conjugated or non-conjugated dendrimers.
  • dendrimer is to be understood in the present application, a highly branched compound consisting of a
  • structural unit in the present application means a unit which, starting from a monomer unit which has at least two, preferably two, reactive groups, is incorporated by reaction under compounding as part of the polymer backbone, and linked thereto present in the produced polymer as a repeat unit.
  • mono- or polycyclic aromatic ring system in the present application means an aromatic ring system having 6 to 60, preferably 6 to 30 and particularly preferably 6 to 24 aromatic ring atoms, which does not necessarily contain only aromatic groups but in which also several aromatic units by a short non-aromatic unit ( ⁇ 10% of H
  • atoms preferably ⁇ 5% of the atoms other than H
  • atoms other than H such as, for example, an sp 3 -hybridized C atom or O- or N- Atom, a CO group, etc.
  • systems such as 9,9' spirobifluorene, 9,9-diarylfluorene and 9,9-dialkylfluoren, be taken to mean aromatic ring systems.
  • the aromatic ring systems may be mono- or polycyclic, ie they may have one ring (eg phenyl) or several rings which may also be condensed (eg naphthyl) or covalently linked (eg biphenyl) or contain a combination of fused and linked rings ,
  • Preferred aromatic ring systems are, for example, phenyl, biphenyl,
  • Terphenyl [1, 1 ': 3', 1 "] terphenyl-2'-yl, quarterphenyl, naphthyl, anthracene, binaphthyl, phenanthrene, dihydrophenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene
  • the term "mono- or polycyclic, heteroaromatic ring system” is understood as meaning an aromatic ring system having 5 to 60, preferably 5 to 30 and particularly preferably 5 to 24 aromatic ring atoms, one or more of these atoms a heteroatom is / are.
  • the "mono- or polycyclic heteroaromatic ring system” does not necessarily include only aromatic
  • heteroaromatic ring systems may be mono- or polycyclic, ie they may have one or more rings, which may also be fused or covalently linked (eg pyridylphenyl), or contain a combination of fused and linked rings. Preference is given to fully conjugated heteroaryl groups.
  • Preferred heteroaromatic ring systems are, for example, 5-membered rings such as pyrrole, pyrazole, imidazole, 1, 2,3-triazole, 1, 2,4-triazole, tetrazole, furan, thiophene, selenophen, oxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, 1, 2,3- Oxadiazole, 1, 2,4-oxadiazole, 1, 2,5-oxadiazole, 1, 3,4-oxadiazole, 1, 2,3-thiadiazole, 1, 2,4-thiadiazole, 1, 2,5-thiadiazole, 1, 3,4-thiadiazole, 6-membered rings such as pyridine, pyridazine, pyrimidine, pyrazine, 1, 3,5-triazine, 1, 2,4-triazine, 1, 2,3-triazine, 1, 2,4 , 5-tetrazine, 1, 2,3,4-tetrazine, 1, 2,
  • the mono- or polycyclic, aromatic or heteroaromatic ring system may be unsubstituted or substituted. Substituted means in the present application that the mono- or polycyclic, aromatic or heteroaromatic ring system has one or more substituents R.
  • Heteroaralkyl having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a Diaryl- amino group, Diheteroarylaminooeuvre or Arylheteroarylaminooeuvre having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a crosslinkable group Q;
  • Two or more radicals R may also together form a monocyclic or polycyclic, aliphatic, aromatic and / or benzoannulated ring system.
  • Preferred alkyl groups having 1 to 10 carbon atoms are shown in the following table:
  • R 1 is preferably identical or different at each occurrence, H, D, F or an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic and / or a heteroaromatic hydrocarbon radical with 5 up to 20 C atoms, in which also one or more H atoms may be replaced by F;
  • substituents R can also be a mono- or polycyclic, aliphatic or
  • R 1 is more preferably identical or different at each occurrence, H, D or an aliphatic hydrocarbon radical having 1 to 20 carbon atoms, an aromatic and / or a heteroaromatic hydrocarbon radical having 5 to 20 carbon atoms; in this case, two or more substituents R 1 can also be a mono- or polycyclic, aliphatic or
  • R is very particularly preferably identical or different at each occurrence, H or an aliphatic hydrocarbon radical having 1 to 10 carbon atoms, an aromatic and / or a heteroaromatic hydrocarbon radical having 5 to 10 carbon atoms.
  • Ar 1 , Ar 3 , Ar 5 , Ar 6 , R, m, n and X may have the meanings given above, and
  • p 0, 1, 2, 3, 4 or 5.
  • the structural units of the formulas (II) and (III) are selected from the structural units of the following formulas (IIa) and (IIIa):
  • Ar 1 , Ar 2 , R, m, n and p may have the meanings given above, and
  • the structural units of the formulas (IV) and (V) are selected from the structural units of the following formulas (IVa) and (Va):
  • Ar 1 , Ar 3 , Ar 5 , R, m, n and X may have the meanings given above.
  • Ar 1 , Ar 2 , R, m, n and p can assume the meanings given above.
  • Ar 1 , Ar 3 , Ar 5 , R, m, n and X may have the meanings given above.
  • Ar 1 , Ar 2 , R, k, m, n and p can assume the meanings given above.
  • the structural units of the formulas (IIa) and (IIIa) are selected from the structural units of the following formulas (IIb) and (IIIb):
  • R, k, m, n and p can assume the meanings given above.
  • the structural units of the formulas (IVa) and (Va) are selected from the structural units of the following formulas (IVb) and (Vb):
  • R, X, k, m, n and p can assume the meanings given above, and
  • s 1 to 20, preferably 1 to 0, is.
  • the structural units of the formulas (VIa) and (VIIa) are selected from the structural units of the following formulas (VIb) and (VIIb):
  • R, X, m and n can assume the meanings given above.
  • R, X, k, m, and n can assume the meanings given above.
  • the proportion of structural units of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII) or (IX) in the polymer is in the range from 1 to 100 mol%.
  • the polymer according to the invention contains only one structural unit of the formula (I), (II), (III), (IV), (V),
  • the polymer according to the invention is a homopolymer.
  • the proportion is
  • Group 1 units containing the hole injection and / or
  • Group 2 units containing the electron injection and / or
  • Group 3 Units that are combinations of individual units of the group
  • Group 4 units which the emission characteristics so far
  • Electrofluorescence can be obtained
  • Group 5 units that transition from singlet to
  • Group 6 Units indicating the emission color of the resulting
  • Group 7 units typically used as polymer backbone
  • Group 8 units containing the film morphology and / or the
  • Preferred polymers according to the invention are those in which
  • At least one structural unit has charge transport properties, i. contain the units from group 1 and / or 2.
  • Have hole transport properties are, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine, phenothiazine, Phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxin, phenoxathiin, carbazole, azulene, thiophene, pyrrole and furan derivatives, and other O, S or N containing heterocycles.
  • Preferred structural units from group 1 are the structural units of the following formulas (1a) to (1 q):
  • Structural unit one or two, preferably two, bonds to
  • the structural unit has one, two or three, preferably two, bonds to adjacent structural units. If four dashed lines are present in the formulas, the structural unit has one, two, three or four, preferably two, bonds to adjacent structural units. They can be arranged independently, identically or differently, in ortho, meta or para position.
  • Group 2 structural units having electron injection and / or electron transport properties are, for example, pyridine, Pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline,
  • the polymers according to the invention comprise units from group 3 in which structures which increase hole mobility and which electron mobility increase (ie units from groups 1 and 2) are directly bonded to one another or contain structures which both the hole mobility and the
  • Some of these units can serve as emitters and shift the emission color to green, yellow or red. Their use is thus suitable, for example, for the production of other emission colors from originally blue-emitting polymers.
  • Group 4 structural units are those which are also included in
  • Group 5 structural units are those which improve the singlet to triplet state transition and which, assisting with the Group 4 structural elements, improve the phosphorescence properties of these structural elements.
  • carbazole and bridged carbazole dimer units are suitable for this purpose, as described, for example, in WO 2004/070772 A2 and WO 2004/1 3468 A1 to be discribed.
  • ketones, phosphine oxides, sulfoxides, sulfones, silane derivatives and similar compounds as described, for example, in WO 2005/040302 A1.
  • Structural units of group 6 are, in addition to those mentioned above, those which have at least one further aromatic or another conjugated structure which is not classified under the above-mentioned. Fall groups, d. H. which only slightly influence the charge carrier mobility, the none
  • organometallic complexes are or which do not affect the
  • Aromatic structures having from 6 to 40 carbon atoms or else toluenes, stilbene or bisstyrylarylene derivatives which may each be substituted by one or more radicals R are preferred. Particularly preferred is the incorporation of 1, 4 or 9,10-anthrylene, 1, 6, 2,7 or 4,9-pyrenylene, 3,9 or 3,10-perylenylene, 4, 4'-tolanylene, 4,4'-stilbenylene, benzothiadiazole and corresponding oxygen derivatives, quinoxaline, phenothiazine,
  • Oligo (thiophenylene), phenazine, rubrene, pentacene or
  • Perylene derivatives which are preferably substituted, or preferably conjugated push-pull systems (systems containing donor and
  • Group 7 structural units are units containing aromatic structures having from 6 to 40 carbon atoms, which are typically used as a backbone polymer. These are, for example, 4,5-dihydropyrene derivatives, 4,5,9,10-tetrahydropyrene derivatives, fluorene derivatives, 9,9'-spirobifluorene derivatives, phenanthrene derivatives, 9,10-dihydrophenanthrene derivatives, 5,7-dihydrodibenzooxepine derivatives and cis- and trans-indenofluorene derivatives but also 1, 2, 1, 3 or 1, 4-phenylene, 1, 2, 1, 3 or 1, 4-naphthylene, 2,2'-, 3,3'- or 4, 4'-biphenylylene, 2,2 ", 3,3" or 4,4 "-terphenyls, 2,2 ', 3,3' or 4,4'-bi-1,1 '-naphthylylene or 2,2 "', 3,3"' or
  • R, k, m, n and p can assume the meanings given above.
  • the dashed lines represent possible bonds to the adjacent structural units in the polymer. If two dashed lines are present in the formulas, then the
  • Structural unit one or two, preferably two, bonds to
  • the structural units have one, two, three or four, preferably two, bonds to adjacent structural units. They can be arranged independently, identically or differently, in ortho, meta or para position.
  • Group 8 structural units are those which affect the film morphology and / or the rheological properties of the polymers, e.g. Siloxanes, alkyl chains or fluorinated groups, but also particularly rigid or flexible units, liquid-crystalline units or crosslinkable groups.
  • polymers according to the invention which, in addition to structural units of the formulas (I), (II), (III), (IV), (V), (VI), (VII), (VIII) and / or (IX), additionally additionally contain one or more units selected from Groups 1 to 8. It may likewise be preferred if more than one further structural unit from a group is present at the same time.
  • Preferred polymers according to the invention are those which have, in addition to at least one structural unit of the formulas (I), (II), (III), (IV), (V), (VI), (VII), (VIII) and / or (IX) still contain units from group 7. It is likewise preferred if the polymers according to the invention
  • Contain units that improve the charge transport or the charge injection ie units from the group 1 and / or 2.
  • the polymers according to the invention are either homopolymers of structural units of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII) or (IX) 10 or copolymers.
  • the polymers of the invention may be linear or branched, preferably linear.
  • Copolymers of the invention may in addition to one or more structural units of the formulas (I), (II), (III), (IV), (V), (VI), (VII), (VIII) and / or (IX) potentially one or several other structures from the groups 1 to 8 listed above.
  • copolymers according to the invention can have random, alternating or block-like structures or alternatively have several of these structures in turn.
  • the copolymers according to the invention particularly preferably have random or alternating structures.
  • the copolymers are random or alternating copolymers. How to obtain copolymers with block-like structures
  • the polymer can also have dendritic structures.
  • the polymers according to the invention contain, in addition to one or more
  • Crosslinkable group Q in the sense of the present invention means a functional group which is able to undergo a reaction and thus form an insoluble compound, the reaction being able to react with another, identical group Q, another, different group Q. or any other part of it or another
  • the crosslinkable group is thus a reactive group.
  • a correspondingly crosslinked compound is obtained.
  • the chemical reaction can also be carried out in the layer, resulting in an insoluble layer.
  • the crosslinking can usually be assisted by heat or by UV, microwave, X-ray or electron radiation, if appropriate in the presence of an initiator.
  • "Insoluble" in the sense of the present invention preferably means that the polymer according to the invention after the crosslinking reaction, ie after the reaction the crosslinkable groups, at room temperature in an organic solvent having a solubility which is at least a factor of 3, preferably at least a factor of 10, lower than that of the corresponding non-crosslinked polymer of the invention in the same organic solvent.
  • the structural unit bearing the crosslinkable group Q may in a first embodiment be selected from the structural units of the formulas (I), (II), (III), (IV), (V), (VI), (VII) , (VIII) and / or (IX).
  • Preferred structural units bearing the crosslinkable group Q are the following, from the structural units of the formulas (I-1a), (1-1b), (1-1c) and (1-1d), respectively, of the structural units of the Formulas (Xla), (Xlb), (Xlc) and (Xld):
  • o, s, t, u and v are each 0 or 1, and the sum (o + s +
  • t + u + v) 1, 2, 3, 4 or 5; preferably 1, 2 or 3; more preferably 1 or 2, and most preferably 1.
  • o, s, t, u, v and w are each 0 or 1, and the sum (o + s +
  • t + u + v + w 1,2,3,4,5 or 6, preferably 1,2,3 or 4, more preferably 1, 2 or 3, and most preferably 1 or 2.
  • the structural units of the formula (IV), (V), (VI) and (VII) can also have crosslinkable groups Q.
  • the structural unit bearing the crosslinkable group Q may be selected from the structural units disclosed in Groups 1-8.
  • a preferred structural unit bearing the crosslinkable group Q is the following structural unit of the formula (XII) derived from the triarylamine units of group 1:
  • Ar 1 , Ar 2 and Ar 3 may have the meanings given above in relation to formula (I).
  • Another preferred structural unit bearing the crosslinkable group Q is the following group 7-derived structural unit of the formula (XIII):
  • the crosslinkable group Q is a functional group capable of undergoing a chemical reaction to form an insoluble polymeric compound. It is generally possible to use all groups Q known to the person skilled in the art for this purpose. In particular, it is the task of this group to link the polymeric compounds according to the invention, if appropriate with further reactive polymeric compounds, by means of a crosslinking reaction. This results in a crosslinked compound or, when the reaction is carried out in one layer, to a crosslinked layer.
  • a crosslinked layer in the sense of the present invention is understood to mean a layer which can be obtained by carrying out the crosslinking reaction from a layer of the crosslinkable, polymeric compound according to the invention.
  • Crosslinking reaction can generally be effected by heat and / or by UV, microwave, X-ray or electron radiation and / or by the use of radical formers, anions, cations, acids and / or Photoacids are initiated. Likewise, the presence of
  • Crosslinkable groups Q preferred in accordance with the invention are those in the
  • Suitable units are a terminal or cyclic double bond, a terminal dienyl group or a
  • terminal triple bond in particular terminal or cyclic alkenyl, terminal dienyl or terminal alkynyl groups having 2 to 40 carbon atoms, preferably having 2 to 10 carbon atoms, wherein also individual CH 2 groups and / or individual H atoms the above groups R can be replaced.
  • alkenyloxy Dienyloxy- or
  • Alkynyloxy groups preferably alkenyloxy groups.
  • acrylic acid units in the broadest sense, preferably acrylic esters, acrylamides, methacrylic esters and
  • Methacrylamides Particularly preferably Ci -10 alkyl acrylate and C 1 0 alkyl methacrylate.
  • the crosslinking reaction of the groups mentioned above under a) to c) can be carried out via a radical, a cationic or an anionic mechanism but also via cycloaddition. It may be useful to add a suitable initiator for the crosslinking reaction.
  • Suitable initiators for free-radical crosslinking are, for example, dibenzoyl peroxide, AIBN or TEMPO.
  • Suitable initiators for the cationic crosslinking are, for example, AICI 3 , BF 3 , triphenylmethyl perchlorate or tropylium hexachloroantimonate.
  • Suitable initiators for the anionic crosslinking are bases, in particular
  • the crosslinking is carried out without the addition of an initiator and is exclusively thermally initiated. This preference is based on the fact that the absence of the initiator prevents contamination of the layer, which could lead to a deterioration of the device properties.
  • crosslinkable groups Q are oxetanes and oxiranes, which crosslink cationically by ring opening.
  • silane groups SiR 3 are also suitable as a class of crosslinkable groups.
  • SiR 3 where at least two groups R, preferably all three groups
  • R is Cl or an alkoxy group having 1 to 20 carbon atoms.
  • crosslinkable groups Q are generally known to those skilled in the art, as are the suitable reaction conditions used to react these groups.
  • Preferred crosslinkable groups Q include alkenyl groups of the following formula Q1, dienyl groups of the following formula Q2,
  • Alkynyl groups of the following formula Q3 alkenyloxy groups of the following formula Q4, dienyloxy groups of the following formulas Q5,
  • Alkynyloxy groups of the following formula Q6 acrylic acid groups of the following formulas Q7 and Q8, oxetane groups of the following formulas Q9 and Q10, oxirane groups of the following formula Q 1 and
  • the radicals R 11 , R 2 and R 3 in the formulas Q1 to Q8 and Q1 1 in each occurrence, identical or different, is H, a straight-chain or branched alkyl group having 1 to 6 C atoms, preferably 1 to 4 C atoms ,
  • the radicals R 11 , R 12 and R 13 are particularly preferably H, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl and very particularly preferably H or methyl.
  • the dashed bond in the formulas Q1 to Q11 and the dashed bonds in the formula Q12 represent the attachment of the crosslinkable group to the structural units.
  • crosslinkable groups of the formulas Q1 to Q12 may be linked directly to the structural unit, or indirectly, via a further, mono- or polycyclic, aromatic or heteroaromatic
  • Ring system Ar 10 as shown in the following formulas Q13 to Q24:
  • Ar 10 in the formulas Q 13 to Q 24 can assume the same meanings as Ar 1 .
  • crosslinkable groups Q are the following:
  • the radicals R 11 and R 2 in the formulas Q7a and Q13a to Q19a in each occurrence, identical or different, are H or a straight-chain or branched alkyl group having 1 to 6 C atoms, preferably 1 to 4 C atoms.
  • the radicals R 1 and R 12 are particularly preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl and very particularly preferably methyl.
  • the radical R 13 in the formulas Q7b and Q19b at each occurrence is a straight-chain or branched alkyl group having 1 to 6 C atoms, preferably 1 to 4 C atoms.
  • the radical R 3 is particularly preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl and very particularly preferably methyl.
  • crosslinkable groups Q are the following:
  • groups Q12, Q12a, Q12b, and Q24 each have two bonds to two having adjacent ring carbon atoms of the structural unit. All other crosslinkable groups merely have a bond to the structural unit.
  • the proportion of crosslinkable structural units in the polymer is in the range from 0.01 to 50 mol%, preferably in the range from 0.1 to 30 mol%, particularly preferably in the range from 0.5 to 20 mol% and very particularly preferably in the range from 1 to 15 mol% based on 100 mol% of all the copolymerized monomers contained in the polymer as structural units.
  • the polymers according to the invention comprising structural units of the formulas (I), (II), (III), (IV), (V), (VI), (VII), (VIII) and / or (IX) are generally prepared by polymerization of one or more types of monomer, of which at least one monomer in the polymer to
  • the CC linkages are preferably selected from the groups of the SUZUKI coupling, the YAMAMOTO coupling and the STILLE coupling; the CN linkage is preferably a HARTWIG-BUCHWALD coupling.
  • the present invention thus also provides a process for the preparation of the polymers according to the invention, which is characterized
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 may assume the meanings given in relation to the structural unit of the formula (I).
  • the monomers of the formulas (MI-1) and (MI-2) which lead to structural units of the formula (1-1) or (I-2) in the polymers according to the invention are compounds which are correspondingly substituted and to two
  • Positions have suitable functionalities that allow to incorporate this monomer unit in the polymer.
  • These monomers of the formulas (MI-1) and (Ml-2) are thus also the subject of the present invention.
  • the group Y represents, for one or the other, one for one Polymerization reaction suitable leaving group, so that the incorporation of the monomer units in polymeric compounds is made possible.
  • Y represents a chemical functionality which is identically or differently selected from the class of halogens, O-tosylates, O-triflates, O-sulfonates, boric acid esters, partially fluorinated silyl groups,
  • the backbone of the monomer compounds can be functionalized by standard methods, for example by Friedel-Crafts alkylation or acylation. Furthermore, the skeleton can be after
  • halo- genated compounds can optionally be further implemented in additional functionalization steps.
  • additional functionalization steps for example, the
  • halogenated compounds are used either directly or after conversion into a boronic acid derivative or organotin derivative as starting materials for the reaction to polymers, oligomers or dendrimers.
  • the polymers of the invention can be used as a pure substance, but also as a mixture together with any other polymeric, oligomeric, dendritic or low molecular weight substances.
  • a low molecular weight substance is understood as meaning compounds having a molecular weight in the range from 100 to 3000 g / mol, preferably 200 to 2000 g / mol. These other substances may e.g. improve the electronic properties or self-emit.
  • Another object of the present invention is thus a polymer blend comprising one or more polymers of the invention, and one or more further polymeric, oligomeric, dendritic and / or low molecular weight substances.
  • the invention further provides solutions and formulations of one or more polymers of the invention or a polymer blend in one or more solvents. How such solutions can be prepared is known to the person skilled in the art and described, for example, in WO 02/072714 A1, WO 03/019694 A2 and the literature cited therein.
  • These solutions can be used to prepare thin polymer layers, for example, by area-coating methods (e.g., spin-coating) or by printing methods (e.g., ink-jet printing).
  • area-coating methods e.g., spin-coating
  • printing methods e.g., ink-jet printing
  • Polymers containing structural units which have a crosslinkable group Q are particularly suitable for the production of films or coatings, in particular for the production of structured
  • Coatings for example by thermal or light-induced in situ polymerization and in situ crosslinking, such as in situ UV photopolymerization or photopatterning.
  • both corresponding polymers can be used in pure substance, but it is also possible to use formulations or mixtures of these polymers as described above. These can be used with or without the addition of solvents and / or binders. Suitable materials, methods and devices for the methods described above are described, for example, in WO 2005/083812 A2.
  • Possible binders are, for example, polystyrene, polycarbonate, poly (meth) acrylates, polyacrylates, polyvinyl butyral and similar, optoelectronically neutral polymers.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -Fenchone, 1, 2,3,5-tetramethylbenzene, 1, 2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4 Dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol,
  • Another object of the present invention is thus the
  • the crosslinkable group more preferably one
  • Vinyl group or alkenyl group is preferably incorporated into the polymer by the WITTIG reaction or a WITTIG analogous reaction. If the crosslinkable group is a vinyl group or alkenyl group, the crosslinking can take place by free-radical or ionic polymerization, which can be induced thermally or by radiation.
  • the free-radical polymerization which is thermally induced is preferably at temperatures of less than 250 ° C, more preferably at temperatures of less than 200 ° C.
  • an additional styrenic monomer is added during the crosslinking process to achieve a higher degree of crosslinking.
  • the proportion of styrene monomer added is in the range of 0.01 to 50 mol%, particularly preferably 0.1 to 30 mol%, based on 100 mol% of all the copolymerized monomers contained in the polymer as structural units.
  • Radical or ionic crosslinking preferably radical crosslinking, which can be induced both thermally and by radiation, preferably thermally.
  • crosslinked polymers produced by the process according to the invention are insoluble in all common solvents. In this way, defined layer thicknesses can be produced, which are also due to the
  • the present invention thus also relates to a crosslinked polymer obtainable by the aforementioned method.
  • the crosslinked polymer is preferably prepared in the form of a crosslinked polymer layer as described above.
  • On the surface of such a crosslinked polymer layer due to the insolubility of the crosslinked polymer in all solvents, another layer of a solvent can be applied by the techniques described above.
  • the present invention also includes so-called hybrid devices in which one or more layers which are processed from solution and layers which are produced by vapor deposition of low molecular weight substances may occur.
  • the polymers according to the invention can be used in electronic or optoelectronic devices or for their preparation.
  • Another object of the present invention is thus the
  • Electroluminescent devices OLED
  • OFETs organic field effect Transistors
  • O-ICs organic integrated circuits
  • TFTs organic thin-film transistors
  • O-SCs organic solar cells
  • O-lasers organic laser diodes
  • O-lasers organic photovoltaic elements or devices or organic photoreceptors (OPCs) , particularly preferably in organic electroluminescent devices (OLED).
  • OLEDs can be produced is known to the person skilled in the art and is described in detail, for example, as a general method in WO 2004/070772 A2, which is to be adapted accordingly for the individual case.
  • the polymers according to the invention are very particularly suitable as electroluminescent materials in OLEDs or displays produced in this way.
  • Active layer means that the layer is able to emit light upon application of an electric field (light-emitting layer) and / or that it improves the injection and / or the transport of the positive and / or negative charges (charge injection or
  • a preferred subject of the present invention is therefore also the use of the polymers according to the invention in OLEDs, in particular as electroluminescent material.
  • the present invention furthermore relates to electronic or optoelectronic components, preferably organic electroluminescent devices (OLED), organic field-effect transistors (OFETs), organic integrated circuits (O-ICs), organic
  • TFTs Thin film transistors
  • O-SCs organic solar cells
  • O-lasers organic laser diodes
  • O-PAV organic photovoltaic
  • OPCs organic photoreceptors
  • the active layer may, for example, be a light-emitting layer, a charge-transport layer and / or a charge-injection layer.
  • the main aim is the use of the polymers according to the invention in relation to OLEDs and corresponding displays.
  • the polymers of the invention as semiconductors for the other, described above
  • alkylated aromatics takes place by means of a Friedel-Crafts reaction in accordance with methods A and B described below by way of example.
  • the mixture is filtered through about 750 g of silica gel, which is washed with about 500 ml of dichloromethane.
  • the yellow solution is completely freed from solvent on a rotary evaporator, the remaining orange solid is stirred with about 2 l of ethanol at 60 ° C.
  • the mixture is cooled to 0 ° C. for 1 h, then the solid is filtered off with suction and washed twice with 300 ml of cold ethanol each time. After drying in a vacuum oven, 827 g (78% of theory) remain as a pale yellow crystalline solid.
  • the pale yellow solution is completely freed from solvent on a rotary evaporator, leaving a yellow oil. This is over a distillation bridge without cooling at 10 "2 mbar and a head temperature of up to 170 ° C of excess 3-chloro-3,7-dimethyioctane and monosubstituted biphenyl freed.
  • the organic phase is washed twice with saturated aqueous sodium thiosulfate solution and twice with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate and freed from the solvent on a rotary evaporator.
  • the residue is taken up in 50 ml of heptane and filtered through about 50 g of silica gel, which is washed with 100 ml of heptane.
  • the solvent is removed on a rotary evaporator.
  • the remaining residue is purified in a short path distillation at 10 -3 mbar and a gradually increased jacket temperature of up to 180 ° C. This leaves 60.6 g (81% of theory) of a yellowish solid.
  • bromides Bro2 and Bro3 can be represented:
  • 7'-dialkylated 4-bromo-9,9-spirobifluorenes can be prepared by reaction of 4,4'-dialkyl-substituted 2-bromobiphenyl and 4-bromofluorenone, as exemplified by the compounds Spi2 and Spi3 shown:
  • the solid is filtered off and washed with toluene.
  • the filtrates are concentrated, stirred hot with ethanol, filtered off with suction and dried together with the precipitated solid in a vacuum oven. It remains 28.3 g (68% of theory) as a yellow solid.
  • the reaction mixture is concentrated. The residue is stirred hot in ethanol.
  • the solid is filtered and recrystallized three times in ethyl acetate (0.8 L each). After sucking off the solid and drying in a vacuum drying oven, it is tempered at 10 ⁇ 5 mbar and 180 ° C. to remove residues of solvents and volatile impurities. This gives 22.0 g (71% of theory) of the product as a yellow powder with a purity of 99.8% by HPLC.
  • Step 1
  • Hot extractor extracted over a bed of alumina (basic, activity level 1). After cooling, the precipitated solid is filtered off, washed twice with about 200 ml of heptane and dried under vacuum. There remain 53.0 g (66% of theory) as a slightly colored solid. Level 2:
  • the mixture is with aqueous sodium hydroxide solution neutral.
  • the organic phase is separated, washed twice with about 350 ml of water and once with 350 ml of saturated sodium chloride solution and dried over magnesium sulfate.
  • the solvent is removed on a rotary evaporator. This leaves a yellow oil that crystallizes within 24 hours.
  • the solid is extracted with about 300 ml of heptane in a continuous hot extractor over a bed of alumina (basic, activity level 1) and filtered off after cooling. It is recrystallized three times from isopropanol. After drying in vacuo, 13.0 g (18% of theory) remain as a yellow solid.
  • N4, N4'-bis-biphenyl-4-yl-N4, N4'-diphenyl-biphenyl-4,4'-diamine (12 mmol) (CAS: 134008-76-7) are dissolved in 1.5 l of dried tetrahydro - Furan (THF) dissolved and cooled to 0 ° C. 40 g of N-bromosuccinimide
  • the solid is filtered through silica gel and Celite and the solution is concentrated.
  • the residue is treated with 800 ml of dichloromethane.
  • the phases are separated.
  • the organic phase is washed three times with 300 ml of water and dried over Na 2 S0 4 , then filtered and concentrated by rotary evaporation.
  • the product is filtered through silica gel (toluene as eluent).
  • the clean fractions (about 35 g) are recrystallized from a mixture of 50 ml of heptane and 170 ml of toluene.
  • the solid is filtered, washed with heptane and dried. This gives 33.5 g (52% of theory) of the product as a colorless powder with a purity of 99.1% by HPLC.
  • Step 1
  • Stage 3 Preparation of Mo16.Br 97.8 g (346 mmol) of 1-bromo-3-iodobenzene, 96.1 g (157 mmol) of 4-amino-2'7'-bis- (37-dimethyloctan-3-yl) -9,9'-spirobifluorene, 2.4 g (12.6 mmol)
  • Heptane extracted for about 16 h After cooling to room temperature, the solid is filtered off with suction and the mother liquor is concentrated to dryness on a rotary evaporator. Both solids are combined and re-extracted as described; the extraction sleeves used are only weakly colored after the second extraction. The mother liquor is concentrated again to dryness and combined with the precipitated solids. It is taken up in about 250 ml of heptane, the suspension is heated to reflux and added dropwise to complete toluene solution (about 190 ml). After cooling to room temperature, the solid formed is filtered off with suction and recrystallized again as described.
  • Polymers Po to Po14 are prepared by SUZUKI coupling according to the method described in WO 2010/097155 from the monomers shown in Part A.
  • these are converted into crosslinkable vinyl groups after the polymerization by means of the WITTIG reaction in accordance with the process described in WO 2010/097155.
  • the polymers listed correspondingly in the following table and used in Part C thus have crosslinkable vinyl groups instead of the aldehyde groups originally present.
  • the palladium and bromine contents of the polymers are determined by ICP-MS. The determined values are below 10 ppm.
  • the molecular weights M w and the polydispersities D are determined by means of gel permeation chromatography (GPC) (Model: Agilent HPLC System Series 1100) (column: PL-RapidH from Polymer Laboratories;
  • Part C Device examples
  • the polymers according to the invention can be processed from solution and, compared to vacuum-processed OLEDs, lead to OLEDs which are much easier to produce and nevertheless have good properties.
  • crosslinkable variants of the polymers according to the invention give a completely insoluble layer after crosslinking is tested analogously to WO 2010/097155.
  • Table C1 shows the remaining layer thickness of the original 20 nm according to the washing process described in WO 2010/097155.
  • the layer thickness does not decrease, the polymer is insoluble and thus the crosslinking is sufficient.
  • the comparative polymer V1 which carries no crosslinking group, hardly crosslinks at 220 ° C.
  • the comparative polymer V2 and the inventive polymers Po01, Po02, Po05, Po13 and Po14 completely crosslink at 220 ° C.
  • the polymers of the invention are in two different
  • Structure A is as follows:
  • HTL Hole transport layer
  • Emission layer (60 nm)
  • HBL hole blocking layer
  • Electron transport layer (ETL) (40 nm),
  • Structure B is as follows:
  • HTL Hole transport layer
  • Emission layer (30 nm)
  • Electron transport layer (20 nm)
  • the substrate used is glass plates coated with structured ITO (indium tin oxide) of thickness 50 nm. For better processing, they are coated with PEDOTPSS. The spin-on takes place in air from water. The layer is baked for 10 minutes at 180 ° C.
  • structured ITO indium tin oxide
  • PEDOTPSS is procured from Heraeus Precious Metals GmbH & Co. KG, Germany. On these coated glass slides are the
  • the compounds of the invention and comparative compounds are used, each dissolved in toluene.
  • the typical Feststoffgehait of such solutions is about 5 g / l, if, as here, the typical for a device layer thicknesses of 20 or 40 nm means Spincoating is to be achieved.
  • the layers are in one
  • Inertgasatmospstone in this case argon, spin-on and baked for 60 minutes at 180 ° C or 220 ° C.
  • the emission layer is always composed of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter). Furthermore, mixtures of several matrix materials and co-dopants can occur.
  • the mixture for the emission layer is dissolved for Structure A in toluene. The typical solids content of such
  • Solutions is about 18 g / l, if, as here, the typical for a device layer thickness of 60nm is to be achieved by spin coating.
  • Layers are spin-coated in an inert gas atmosphere, in this case argon, and baked at 180 ° C. for 10 minutes.
  • the emission layer is formed by thermal evaporation in a
  • the layer may consist of more than one material, the other by co-evaporation in one
  • H3 Dotand (95%: 5%) means here that the materials H3 and dopant are present in a volume fraction of 95%: 5% in the layer.
  • the materials for the hole blocking layer and electron transport layer are also thermally evaporated in a vacuum chamber and are shown in Table C3.
  • the hole blocking layer consists of ETM1.
  • the electron transport layer consists of the two materials ETM1 and ETM2, which are admixed by co-evaporation in a volume fraction of 50% each.
  • the cathode is formed by the thermal evaporation of a 100nm thick aluminum layer.
  • the OLEDs are characterized by default.
  • the electroluminescence spectra, current-voltage-luminance characteristics are determined assuming a lambertian radiation characteristic and the (operating) life. Key figures are determined from the lUL characteristic curves, such as the operating voltage (in V) and the external quantum efficiency (in%) at a specific brightness.
  • LD50 @ 1000cd / m 2 is the lifetime until the OLED has dropped to 50% of the initial intensity, ie 500 cd / m 2 , at a starting brightness of 1000 cd / m 2 .
  • LD80 @ 0000cd / m 2 is the lifetime until the OLED has dropped to 80% of the initial intensity, ie 8000 cd / m 2 , at a starting brightness of 10000 cd / m 2 .
  • the polymers according to the invention when used as hole transport layers in OLEDs, give improvements over the prior art, in particular with regard to service life and operational stress. Green and blue emitting OLEDs are produced with the materials according to the invention.

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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
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  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

Abstract

L'invention concerne des polymères contenant des unités répétitives oligo-triarylamine substituées en position ortho, des procédés de préparation de ces polymères et leur utilisation dans des dispositifs électroniques, notamment dans des dispositifs électroluminescents organiques, appelés OLED (diodes électroluminescentes organiques). L'invention concerne également des dispositifs électroluminescents organiques contenant ces polymères.
EP13717171.6A 2012-04-17 2013-04-15 Polymères contenant des unités oligo-triarylamine substituées et dispositifs électroluminescents contenant ces polymères Active EP2838930B1 (fr)

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CN104245784B (zh) 2018-08-31
WO2013156130A1 (fr) 2013-10-24
JP2015514839A (ja) 2015-05-21
KR102040350B1 (ko) 2019-11-04
US9745420B2 (en) 2017-08-29
CN104245785B (zh) 2018-05-25
EP2838930B1 (fr) 2020-10-14
JP2015519424A (ja) 2015-07-09
KR102055120B1 (ko) 2019-12-12
CN104245785A (zh) 2014-12-24
JP2018021187A (ja) 2018-02-08
KR102055118B1 (ko) 2019-12-12
EP2838931A1 (fr) 2015-02-25
JP6430367B2 (ja) 2018-11-28
JP2015516487A (ja) 2015-06-11
WO2013156129A1 (fr) 2013-10-24
JP6352245B2 (ja) 2018-07-04
US9815940B2 (en) 2017-11-14
CN104245784A (zh) 2014-12-24
EP2838929A1 (fr) 2015-02-25
US9644070B2 (en) 2017-05-09
US20150069303A1 (en) 2015-03-12
KR20150008126A (ko) 2015-01-21
US20150076415A1 (en) 2015-03-19
KR20150008119A (ko) 2015-01-21
TWI586699B (zh) 2017-06-11
CN104271632B (zh) 2018-08-31
TW201406810A (zh) 2014-02-16
JP2018039984A (ja) 2018-03-15
US20150108408A1 (en) 2015-04-23
WO2013156125A1 (fr) 2013-10-24
JP6305982B2 (ja) 2018-04-04
CN104271632A (zh) 2015-01-07
JP6657146B2 (ja) 2020-03-04
KR20150010737A (ko) 2015-01-28
EP2838929B1 (fr) 2023-06-14
JP6567612B2 (ja) 2019-08-28

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